Triethylamine → Carbamic acid, N-[2-(3-methoxyphenyl)ethyl]-, ethyl ester

HRID 1014300Notes

Reaction equation

HRID 1014300 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[CH3:19][CH2:20][O:21][C:22](Cl)=[O:23]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][C:22](=[O:23])[O:21][CH2:20][CH3:19])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 748663-Methoxyphenethylamine

Product 1

HCID 10822969Carbamic acid, N-[2-(3-methoxyphenyl)ethyl]-, ethyl esterYield 108.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {2-[3-(methyloxy)phenyl]ethyl}amine (20 g, 132.3 mmol) and triethylamine (20 g, 198 mmol) in dichloromethane (150 mL) was added ethyl chloridocarbonate (17.7 g, 163 mmol) dropwise at 0° C. After being stirred for 1 h the solvent was removed under vacuum and the residue was washed with ethyl acetate. Following filtration, the filtrate was concentrated to afford ethyl {2-[3-(methyloxy)phenyl]ethyl}carbamate (32 g, crude, 100%). 1H NMR(CDCl3) δ: 7.15-7.25 (1H), 6.7-6.8 (3H), 4.72 (1H), 3.75 (3H), 3.4 (2H), 2.75 (2H), 2.0 (3H), 1.15-1.3(2H).

Workup

  1. customwas removed under vacuum
  2. washthe residue was washed with ethyl acetate
  3. filtrationfiltration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a1e7108340b4404e93f709d7e29d0b80
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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